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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:35:00 UTC

Update Date

2022-03-07 02:54:55 UTC

HMDB ID

HMDB0036443

Secondary Accession Numbers

HMDB36443

Metabolite Identification

Common Name

Rotundone

Description

Rotundone belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a significant number of articles have been published on Rotundone.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0036443
     RDKit          3D
Rotundone
 38 39  0  0  0  0  0  0  0  0999 V2000
    3.7196   -0.8027    0.3084 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9083    0.0975   -0.2315 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5229    1.4104   -0.6014 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4502   -0.1697   -0.4693 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1926   -1.5982   -0.1605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1724   -2.0197   -0.7238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1370   -1.8571    0.4232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2963   -2.7695    0.2280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5160   -0.4199    0.4506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7470    0.6417    0.4486 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7116    0.8396    0.3238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6150    1.8362    0.6148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2083    2.9750   -0.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9967    1.3902    0.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9265   -0.0623    0.4865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9409   -0.7705    0.7157 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3658   -1.8038    0.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7680   -0.6050    0.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1999    1.2114   -1.4482 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7914    2.1723   -0.8631 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1437    1.8090    0.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3091   -0.0342   -1.5638 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2967   -1.8755    0.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9252   -2.2185   -0.7315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1643   -3.0820   -1.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4219   -1.3447   -1.5704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6156   -2.1478    1.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9312   -3.7857   -0.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9835   -2.4614   -0.5811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8863   -2.8881    1.1778 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1994    0.9722    1.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8937    1.8277   -0.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5858    2.0988    1.6917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6987    2.6546   -1.2001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0998    3.5685   -0.6006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5912    3.6794    0.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1428    1.6118   -0.8754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7210    1.9200    0.8430 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 11  4  1  0
 15  9  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
M  END

Rotundone
  Mrv1572001071617132D          
  Mrv0541 01161311182D          
 16 17  0  0  0  0            999 V2000
   -0.5033    0.7510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2483   -0.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7333   -0.7011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2483   -1.3685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5033   -2.1531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5363   -1.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5363   -0.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1813    0.2258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9856    0.0422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3436   -0.7011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9856   -1.4444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1813   -1.6280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9977   -2.4323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5000    0.6872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1986    1.4552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3158    0.5643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036443

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CC(=O)C2=C1CC(CCC2C)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O/c1-9(2)12-6-5-10(3)15-13(8-12)11(4)7-14(15)16/h10-12H,1,5-8H2,2-4H3

> <INCHI_KEY>
NUWMTBMCSQWPDG-UHFFFAOYSA-N

> <FORMULA>
C15H22O

> <MOLECULAR_WEIGHT>
218.34

> <EXACT_MASS>
218.167065328

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
26.541364361139472

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,8-dimethyl-5-(prop-1-en-2-yl)-1,2,3,4,5,6,7,8-octahydroazulen-1-one

> <ALOGPS_LOGP>
4.04

> <JCHEM_LOGP>
3.7953401820000003

> <ALOGPS_LOGS>
-3.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.970019100795243

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
67.9525

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.11e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,8-dimethyl-5-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydro-2H-azulen-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0036443
     RDKit          3D
Rotundone
 38 39  0  0  0  0  0  0  0  0999 V2000
    3.7196   -0.8027    0.3084 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9083    0.0975   -0.2315 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5229    1.4104   -0.6014 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4502   -0.1697   -0.4693 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1926   -1.5982   -0.1605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1724   -2.0197   -0.7238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1370   -1.8571    0.4232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2963   -2.7695    0.2280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5160   -0.4199    0.4506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7470    0.6417    0.4486 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7116    0.8396    0.3238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6150    1.8362    0.6148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2083    2.9750   -0.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9967    1.3902    0.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9265   -0.0623    0.4865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9409   -0.7705    0.7157 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3658   -1.8038    0.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7680   -0.6050    0.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1999    1.2114   -1.4482 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7914    2.1723   -0.8631 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1437    1.8090    0.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3091   -0.0342   -1.5638 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2967   -1.8755    0.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9252   -2.2185   -0.7315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1643   -3.0820   -1.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4219   -1.3447   -1.5704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6156   -2.1478    1.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9312   -3.7857   -0.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9835   -2.4614   -0.5811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8863   -2.8881    1.1778 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1994    0.9722    1.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8937    1.8277   -0.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5858    2.0988    1.6917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6987    2.6546   -1.2001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0998    3.5685   -0.6006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5912    3.6794    0.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1428    1.6118   -0.8754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7210    1.9200    0.8430 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 11  4  1  0
 15  9  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
M  END

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Rotundone                                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  C   UNK     0      -0.939   1.402   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.463  -0.063   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.369  -1.309   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.463  -2.555   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.939  -4.019   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.001  -2.079   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.001  -0.539   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.205   0.421   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.706   0.079   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.375  -1.309   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.706  -2.696   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.205  -3.039   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.862  -4.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.667   1.283   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.104   2.716   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.189   1.053   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   12                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    6   13                                                  
CONECT   13   12                                                            
CONECT   14    9   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0036443
HETATM    1  C1  UNL     1       3.720  -0.803   0.308  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.908   0.098  -0.232  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.523   1.410  -0.601  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.450  -0.170  -0.469  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.193  -1.598  -0.160  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.172  -2.020  -0.724  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.137  -1.857   0.423  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.296  -2.769   0.228  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.516  -0.420   0.451  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.747   0.642   0.449  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.712   0.840   0.324  1.00  0.00           C  
HETATM   12  C12 UNL     1      -1.615   1.836   0.615  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.208   2.975  -0.281  1.00  0.00           C  
HETATM   14  C14 UNL     1      -2.997   1.390   0.186  1.00  0.00           C  
HETATM   15  C15 UNL     1      -2.926  -0.062   0.487  1.00  0.00           C  
HETATM   16  O1  UNL     1      -3.941  -0.770   0.716  1.00  0.00           O  
HETATM   17  H1  UNL     1       3.366  -1.804   0.617  1.00  0.00           H  
HETATM   18  H2  UNL     1       4.768  -0.605   0.474  1.00  0.00           H  
HETATM   19  H3  UNL     1       4.200   1.211  -1.448  1.00  0.00           H  
HETATM   20  H4  UNL     1       2.791   2.172  -0.863  1.00  0.00           H  
HETATM   21  H5  UNL     1       4.144   1.809   0.233  1.00  0.00           H  
HETATM   22  H6  UNL     1       1.309  -0.034  -1.564  1.00  0.00           H  
HETATM   23  H7  UNL     1       1.297  -1.875   0.903  1.00  0.00           H  
HETATM   24  H8  UNL     1       1.925  -2.219  -0.731  1.00  0.00           H  
HETATM   25  H9  UNL     1      -0.164  -3.082  -1.007  1.00  0.00           H  
HETATM   26  H10 UNL     1      -0.422  -1.345  -1.570  1.00  0.00           H  
HETATM   27  H11 UNL     1      -0.616  -2.148   1.361  1.00  0.00           H  
HETATM   28  H12 UNL     1      -1.931  -3.786  -0.024  1.00  0.00           H  
HETATM   29  H13 UNL     1      -2.983  -2.461  -0.581  1.00  0.00           H  
HETATM   30  H14 UNL     1      -2.886  -2.888   1.178  1.00  0.00           H  
HETATM   31  H15 UNL     1       1.199   0.972   1.315  1.00  0.00           H  
HETATM   32  H16 UNL     1       0.894   1.828  -0.195  1.00  0.00           H  
HETATM   33  H17 UNL     1      -1.586   2.099   1.692  1.00  0.00           H  
HETATM   34  H18 UNL     1      -0.699   2.655  -1.200  1.00  0.00           H  
HETATM   35  H19 UNL     1      -2.100   3.569  -0.601  1.00  0.00           H  
HETATM   36  H20 UNL     1      -0.591   3.679   0.327  1.00  0.00           H  
HETATM   37  H21 UNL     1      -3.143   1.612  -0.875  1.00  0.00           H  
HETATM   38  H22 UNL     1      -3.721   1.920   0.843  1.00  0.00           H  
CONECT    1    2    2   17   18
CONECT    2    3    4
CONECT    3   19   20   21
CONECT    4    5   11   22
CONECT    5    6   23   24
CONECT    6    7   25   26
CONECT    7    8    9   27
CONECT    8   28   29   30
CONECT    9   10   10   15
CONECT   10   11   12
CONECT   11   31   32
CONECT   12   13   14   33
CONECT   13   34   35   36
CONECT   14   15   37   38
CONECT   15   16   16
END

HMDB0036443
     RDKit          3D
Rotundone
 38 39  0  0  0  0  0  0  0  0999 V2000
    3.7196   -0.8027    0.3084 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9083    0.0975   -0.2315 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5229    1.4104   -0.6014 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4502   -0.1697   -0.4693 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1926   -1.5982   -0.1605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1724   -2.0197   -0.7238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1370   -1.8571    0.4232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2963   -2.7695    0.2280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5160   -0.4199    0.4506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7470    0.6417    0.4486 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7116    0.8396    0.3238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6150    1.8362    0.6148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2083    2.9750   -0.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9967    1.3902    0.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9265   -0.0623    0.4865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9409   -0.7705    0.7157 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3658   -1.8038    0.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7680   -0.6050    0.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1999    1.2114   -1.4482 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7914    2.1723   -0.8631 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1437    1.8090    0.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3091   -0.0342   -1.5638 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2967   -1.8755    0.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9252   -2.2185   -0.7315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1643   -3.0820   -1.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4219   -1.3447   -1.5704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6156   -2.1478    1.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9312   -3.7857   -0.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9835   -2.4614   -0.5811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8863   -2.8881    1.1778 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1994    0.9722    1.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8937    1.8277   -0.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5858    2.0988    1.6917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6987    2.6546   -1.2001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0998    3.5685   -0.6006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5912    3.6794    0.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1428    1.6118   -0.8754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7210    1.9200    0.8430 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 11  4  1  0
 15  9  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂O

Average Molecular Weight

218.34

Monoisotopic Molecular Weight

218.167065328

IUPAC Name

3,8-dimethyl-5-(prop-1-en-2-yl)-1,2,3,4,5,6,7,8-octahydroazulen-1-one

Traditional Name

3,8-dimethyl-5-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydro-2H-azulen-1-one

CAS Registry Number

18374-76-0

SMILES

CC1CC(=O)C2=C1CC(CCC2C)C(C)=C

InChI Identifier

InChI=1S/C15H22O/c1-9(2)12-6-5-10(3)15-13(8-12)11(4)7-14(15)16/h10-12H,1,5-8H2,2-4H3

InChI Key

NUWMTBMCSQWPDG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036443)

Source

Endogenous

Endogenous (HMDB: HMDB0036443)

Plant

Plant (HMDB: HMDB0036443)

Animal

Animal (HMDB: HMDB0036443)

Exogenous

Food

Food (HMDB: HMDB0036443)

Vegetable

Fruit vegetable

Pepper (FooDB: FOOD00040)

Root vegetable

Root vegetables (FooDB: FOOD00873)

Beverage

Fermented beverage

Grape wine (FooDB: FOOD00612)

Exogenous (HMDB: HMDB0036443)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036443)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036443)

Lipid metabolism pathway (HMDB: HMDB0036443)

Cellular process

Cell signaling (HMDB: HMDB0036443)

Biochemical process

Lipid transport (HMDB: HMDB0036443)

Role

Biological role

Energy source (HMDB: HMDB0036443)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036443)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.98 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.11 g/L	ALOGPS
logP	4.04	ALOGPS
logP	3.8	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	67.95 m³·mol⁻¹	ChemAxon
Polarizability	26.54 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	152.634	31661259
DarkChem	[M-H]-	148.214	31661259
DeepCCS	[M+H]+	153.954	30932474
DeepCCS	[M-H]-	151.596	30932474
DeepCCS	[M-2H]-	185.438	30932474
DeepCCS	[M+Na]+	160.448	30932474
AllCCS	[M+H]+	151.1	32859911
AllCCS	[M+H-H2O]+	147.2	32859911
AllCCS	[M+NH4]+	154.7	32859911
AllCCS	[M+Na]+	155.7	32859911
AllCCS	[M-H]-	158.7	32859911
AllCCS	[M+Na-2H]-	159.1	32859911
AllCCS	[M+HCOO]-	159.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.6 minutes	32390414
Predicted by Siyang on May 30, 2022	17.9554 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.15 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2549.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	613.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	228.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	306.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	177.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	653.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	845.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	80.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1368.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	506.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1464.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	421.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	423.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	363.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	559.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	9.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Rotundone	CC1CC(=O)C2=C1CC(CCC2C)C(C)=C	2305.1	Standard polar	33892256
Rotundone	CC1CC(=O)C2=C1CC(CCC2C)C(C)=C	1718.2	Standard non polar	33892256
Rotundone	CC1CC(=O)C2=C1CC(CCC2C)C(C)=C	1729.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Rotundone,1TMS,isomer #1	C=C(C)C1CCC(C)C2=C(C1)C(C)C=C2O[Si](C)(C)C	1851.8	Semi standard non polar	33892256
Rotundone,1TMS,isomer #1	C=C(C)C1CCC(C)C2=C(C1)C(C)C=C2O[Si](C)(C)C	1762.0	Standard non polar	33892256
Rotundone,1TBDMS,isomer #1	C=C(C)C1CCC(C)C2=C(C1)C(C)C=C2O[Si](C)(C)C(C)(C)C	2066.8	Semi standard non polar	33892256
Rotundone,1TBDMS,isomer #1	C=C(C)C1CCC(C)C2=C(C1)C(C)C=C2O[Si](C)(C)C(C)(C)C	1934.6	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Rotundone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fb9-7930000000-f41b58dbffe47cd961d3	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rotundone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rotundone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rotundone 10V, Positive-QTOF	splash10-014i-0290000000-b4f3ffccd9908e72609d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rotundone 20V, Positive-QTOF	splash10-016r-1950000000-102fce150de6a306ef49	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rotundone 40V, Positive-QTOF	splash10-1001-9610000000-ec36640abe14173fc7be	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rotundone 10V, Negative-QTOF	splash10-014i-0090000000-6271c68eed652c012a8f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rotundone 20V, Negative-QTOF	splash10-014i-0190000000-b9a0009456e23bcff096	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rotundone 40V, Negative-QTOF	splash10-0f76-6920000000-fb0971a924abbb7db989	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rotundone 10V, Positive-QTOF	splash10-014i-0390000000-626b704bc7a58edaf5d3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rotundone 20V, Positive-QTOF	splash10-05rs-2910000000-c915a64affda84373690	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rotundone 40V, Positive-QTOF	splash10-0a4i-5900000000-591237cb80f0c863d5b9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rotundone 10V, Negative-QTOF	splash10-014i-0090000000-868e2fb00a2cfbf6c529	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rotundone 20V, Negative-QTOF	splash10-014i-0190000000-ab85dae8587f91154ad4	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rotundone 40V, Negative-QTOF	splash10-006t-0910000000-89931e0a94b89a4b87a0	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Rotundone

METLIN ID

Not Available

PubChem Compound

12315073

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1081281

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Rotundone (HMDB0036443)

MOL for HMDB0036443 (Rotundone)

3D MOL for HMDB0036443 (Rotundone)

3D SDF for HMDB0036443 (Rotundone)

3D-SDF for HMDB0036443 (Rotundone)

PDB for HMDB0036443 (Rotundone)

3D PDB for HMDB0036443 (Rotundone)

SMILES for HMDB0036443 (Rotundone)

INCHI for HMDB0036443 (Rotundone)

Structure for HMDB0036443 (Rotundone)

3D Structure for HMDB0036443 (Rotundone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra